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In the crystal structure of the title compound, C3H5NO, the mol­ecules are linked through N—H...O hydrogen bonds, forming a two-dimensional supra­molecular network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024816/at2300sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024816/at2300Isup2.hkl
Contains datablock I

CCDC reference: 651529

Key indicators

  • Single-crystal X-ray study
  • T = 113 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.041
  • wR factor = 0.107
  • Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

In order to establish control over the preparation of crystalline solid materials so that their architecture and properties are predictable (Belloni et al., 2005; Tynan et al., 2005; Parashar et al., 1988), the synthesis of new and designed crystal structures has become a major strand of modern chemistry. Metal complexes based on Schiff bases have attracted much attention because they can be utilized as model compounds of the active centres in various proteins and enzymes (Kahwa et al., 1986; Santos et al., 2001). As part of an investigation of the coordination properties of Shiff bases functioning as ligands, we report the synthesis and crystal structure of the title compound, (I).

The expected geometric parameters are observed in (I) (Fig. 1). The molecules are linked through N—H···O hydrogen bonds (Table 2), forming a two-dimensional supramolecular network which leads to stable crystal structure. Fig. 2 shows a portion of this extensively hydrogen-bonded supramolecular assembly.

Related literature top

For related literature, see: Belloni et al. (2005); Kahwa et al. (1986); Parashar et al. (1988); Santos et al. (2001); Tynan et al. (2005).

Experimental top

Acrylamide (1 g) was added to a Trichloro-methane (50 ml), with stirring at 350 K. The resulting colourless solution was filtered and the filtrate was allowed to stand in air at room temperature for 10 d, yielding colourless crystals of (I).

Refinement top

The H atoms of the NH2 group were found from a difference Fourier map and refined freely. C-bound H atoms were placed in calculated positions with C—H = 0.93 Å and refined using a riding model, with Uiso(H) = 1.2Ueq(C).

Structure description top

In order to establish control over the preparation of crystalline solid materials so that their architecture and properties are predictable (Belloni et al., 2005; Tynan et al., 2005; Parashar et al., 1988), the synthesis of new and designed crystal structures has become a major strand of modern chemistry. Metal complexes based on Schiff bases have attracted much attention because they can be utilized as model compounds of the active centres in various proteins and enzymes (Kahwa et al., 1986; Santos et al., 2001). As part of an investigation of the coordination properties of Shiff bases functioning as ligands, we report the synthesis and crystal structure of the title compound, (I).

The expected geometric parameters are observed in (I) (Fig. 1). The molecules are linked through N—H···O hydrogen bonds (Table 2), forming a two-dimensional supramolecular network which leads to stable crystal structure. Fig. 2 shows a portion of this extensively hydrogen-bonded supramolecular assembly.

For related literature, see: Belloni et al. (2005); Kahwa et al. (1986); Parashar et al. (1988); Santos et al. (2001); Tynan et al. (2005).

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The crystal packing of (I), viewed down the a axis. Hydrogen bonds are indicated by dashed lines.
Acrylamide top
Crystal data top
C3H5NOF(000) = 152
Mr = 71.08Dx = 1.187 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1254 reflections
a = 8.2062 (16) Åθ = 2.3–25.0°
b = 5.7480 (11) ŵ = 0.09 mm1
c = 9.0527 (18) ÅT = 113 K
β = 111.37 (3)°Block, colourless
V = 397.65 (16) Å30.10 × 0.08 × 0.06 mm
Z = 4
Data collection top
Rigaku Saturn
diffractometer
943 independent reflections
Radiation source: rotating anode832 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.030
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 2.9°
ω scansh = 1010
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 67
Tmin = 0.991, Tmax = 0.995l = 1111
2936 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.0533P)2 + 0.053P]
where P = (Fo2 + 2Fc2)/3
943 reflections(Δ/σ)max < 0.001
54 parametersΔρmax = 0.20 e Å3
3 restraintsΔρmin = 0.19 e Å3
Crystal data top
C3H5NOV = 397.65 (16) Å3
Mr = 71.08Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.2062 (16) ŵ = 0.09 mm1
b = 5.7480 (11) ÅT = 113 K
c = 9.0527 (18) Å0.10 × 0.08 × 0.06 mm
β = 111.37 (3)°
Data collection top
Rigaku Saturn
diffractometer
943 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
832 reflections with I > 2σ(I)
Tmin = 0.991, Tmax = 0.995Rint = 0.030
2936 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0423 restraints
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.11Δρmax = 0.20 e Å3
943 reflectionsΔρmin = 0.19 e Å3
54 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.01963 (11)0.26267 (14)0.86873 (9)0.0303 (3)
N10.21481 (13)0.36721 (18)1.10725 (11)0.0281 (3)
C10.15782 (14)0.2263 (2)0.98265 (12)0.0226 (3)
C20.26969 (15)0.0222 (2)0.98707 (13)0.0283 (3)
H20.37540.00581.07190.034*
C30.22422 (19)0.1360 (2)0.87512 (16)0.0383 (4)
H3A0.11890.12200.78960.046*
H3B0.29720.26230.88120.046*
H1A0.3147 (13)0.344 (2)1.1876 (13)0.032 (3)*
H1B0.1520 (16)0.492 (2)1.1129 (17)0.041 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0228 (4)0.0377 (6)0.0219 (4)0.0031 (3)0.0021 (3)0.0051 (3)
N10.0226 (5)0.0298 (6)0.0221 (5)0.0056 (4)0.0034 (4)0.0023 (4)
C10.0191 (5)0.0277 (6)0.0189 (5)0.0011 (4)0.0045 (4)0.0016 (4)
C20.0284 (6)0.0317 (7)0.0256 (6)0.0058 (5)0.0109 (5)0.0057 (5)
C30.0482 (8)0.0314 (7)0.0399 (7)0.0052 (6)0.0215 (7)0.0008 (5)
Geometric parameters (Å, º) top
O1—C11.2413 (14)C2—C31.3106 (18)
N1—C11.3275 (14)C2—H20.9300
N1—H1A0.886 (8)C3—H3A0.9300
N1—H1B0.894 (8)C3—H3B0.9300
C1—C21.4815 (16)
C1—N1—H1A122.6 (9)C3—C2—C1121.98 (12)
C1—N1—H1B120.3 (9)C3—C2—H2119.0
H1A—N1—H1B117.1 (11)C1—C2—H2119.0
O1—C1—N1122.39 (11)C2—C3—H3A120.0
O1—C1—C2121.69 (10)C2—C3—H3B120.0
N1—C1—C2115.93 (10)H3A—C3—H3B120.0
O1—C1—C2—C33.48 (18)N1—C1—C2—C3176.71 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.89 (1)1.97 (1)2.8465 (16)170 (1)
N1—H1B···O1ii0.89 (1)2.04 (1)2.9291 (13)171 (2)
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x, y+1, z+2.

Experimental details

Crystal data
Chemical formulaC3H5NO
Mr71.08
Crystal system, space groupMonoclinic, P21/n
Temperature (K)113
a, b, c (Å)8.2062 (16), 5.7480 (11), 9.0527 (18)
β (°) 111.37 (3)
V3)397.65 (16)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.10 × 0.08 × 0.06
Data collection
DiffractometerRigaku Saturn
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.991, 0.995
No. of measured, independent and
observed [I > 2σ(I)] reflections
2936, 943, 832
Rint0.030
(sin θ/λ)max1)0.657
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.107, 1.11
No. of reflections943
No. of parameters54
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.20, 0.19

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.886 (8)1.970 (8)2.8465 (16)169.9 (14)
N1—H1B···O1ii0.894 (8)2.044 (8)2.9291 (13)170.6 (15)
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x, y+1, z+2.
 

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